An internal standard for the quantification of imazalil
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Unlabeled Version(s)
25815Imazalil
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Imazalil-d5 (sulfate)

Item No. 39261

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2-((allyl-d5)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole, monosulfate
CAS Number
1398065-92-3
Synonyms
  • Enilconazole-d5
  • (±)-Imazalil-d5
Molecular Formula
C14H9Cl2D5N2O • H2SO4
Formula Weight
400.3
Purity
≥99% deuterated forms (d1-d5)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
SMILES
ClC1=CC(Cl)=CC=C1C(CN2C=NC=C2)OC([2H])([2H])/C([2H])=C([2H])/[2H].OS(=O)(O)=O
InChi Code
InChI=1S/C14H14Cl2N2O.H2O4S/c1-2-7-19-14(9-18-6-5-17-10-18)12-4-3-11(15)8-13(12)16;1-5(2,3)4/h2-6,8,10,14H,1,7,9H2;(H2,1,2,3,4)/i1D2,2D,7D2;
InChi Key
XVTXMTOYQVRHSK-XXANSLCBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Imazalil-d5 (sulfate) is intended for use as an internal standard for the quantification of imazalil (Item No. 25815) by GC- or LC-MS. Imazalil is an imidazole fungicide that inhibits ergosterol biosynthesis.1 Imazalil inhibits the growth of various fungi in vitro including P. italicum, A. niger, U. maydis, B. alii, and C. cucumerinum in a pH-dependent manner (MICs = 0.005-2 μg/ml at pH 7).2 It inhibits S. cerevisiae, but not rat liver microsomal, cytochrome P450 enzymes (CYPs; IC50s = 0.088 and 80 μM, respectively), as well as aromatase CYP19 from human placental microsomes (IC50 = 0.34 μM).1,3 Imazalil activates the murine pregnane X receptor (PXR) in a concentration-dependent manner in a cell-based reporter assay.4 It increases hepatic CYP3A11 and CYP2B10 mRNA levels in mice when administered at a dose of 100 mg/kg. Imazalil also increases Ki-67-positive nuclei in liver sections and hepatic MCM2 mRNA levels, markers of cell proliferation, in mice when co-administered with the murine constitutive androstane receptor (mCAR) agonist TCPOBOP (Item No. 14140). Formulations containing imazalil have been used to control fungal infection in agriculture.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vanden Bossche, H., Lauwers, W., Willemsens, G., et al. Molecular basis for the antimycotic and antibacterial activity of N-substituted imidazoles and triazoles: The inhibition of isoprenoid biosynthesis. Pestic. Sci. 15(2), 188-198 (1984).

    2. Siegel, M.R., Kerkenaar, A., and Kaars Sijpesteijn, A. Antifungal activity of the systemic fungicide imazalil. Neth. J. Pl. Path. 83(Suppl. 1), 121-133 (1977).

    3. Vinggaard, A.M., Hnida, C., Breinholt, V., et al. Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro. Toxicol. In Vitro 14(3), 227-234 (2000).

    4. Yoshimaru, S., Shizu, R., Tsuruta, S., et al. Acceleration of murine hepatocyte proliferation by imazalil through the activation of nuclear receptor PXR. J. Toxicol. Sci. 43(7), 443-450 (2018).